1,3,5-tris[4'-(tosyloxy)-2'-oxa-1'-butyl]benzene | 152065-65-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 1,3,5-tris[4'-(tosyloxy)-2'-oxa-1'-butyl]benzene
• 英文别名: 2-[[3,5-Bis[2-(4-methylphenyl)sulfonyloxyethoxymethyl]phenyl]methoxy]ethyl 4-methylbenzenesulfonate
• CAS: 152065-65-1
• 化学式: C₃₆H₄₂O₁₂S₃
• 分子量: 762.92
• InChiKey: NFRDYUOJMGREQR-UHFFFAOYSA-N

物化性质

• 沸点：
  857.9±65.0 °C(predicted)
• 密度：
  1.308±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  51
• 可旋转键数：
  21
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  183
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  [10,20-is(3,5-di-tert-butyl)phenyl-5-(3’-hydroxy)phenyl]porphyrin 、 1,3,5-tris[4'-(tosyloxy)-2'-oxa-1'-butyl]benzene 在 sodium hydroxide 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 36.0h， 生成
  参考文献：
  名称：

  分子内内消旋-内消旋偶联合成三维排列的卟啉阵列

  摘要：

  报道了通过空间电子通信的三维排列的卟啉阵列的合成和光物理性质。1,3,5-三氧杂甲撑亚苯基桥连的Zn（II）卟啉三聚体3通过Ag（I）促进的氧化偶联反应偶联，得到包含三个内消旋-内消旋二卟啉的卟啉笼5，然后用DDQ和Sc氧化将其转化（OTf）3进入包含三个稠合的双卟啉的卟啉笼7中。分子内内消旋-内消旋偶联反应应用于卟啉五聚体11，以提供卟啉阵列12由一个卟啉核心和两个介孔组成-介链的双卟啉。用DDQ和Sc（OTf）3进一步氧化12，得到三重堆叠的卟啉阵列13，其由两侧带有两个卟啉带的卟啉芯组成。UV-VIS-NIR吸收和荧光光谱的5，7，12，和13显示了堆叠的卟啉阵列内的扭曲构象和电子交互。

  DOI：

  10.1016/j.tet.2007.05.075
• 作为产物：
  描述：

  均三苄醇 在 盐酸 、 sodium hydroxide 、 sodium hydride 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 146.0h， 生成 1,3,5-tris[4'-(tosyloxy)-2'-oxa-1'-butyl]benzene
  参考文献：
  名称：

  Novel benzene-bridged macrobi- and macrotricyclic polyethers

  摘要：

  Novel three-dimensional benzene-bridged macrobicyclic polyether 1 and macrotricyclic polyether 2 have been prepared. Macrobicyclic triply bridged cyclophane crown compound 1 was synthesized by a tripode-tripode coupling of 1,3,5-tris[7'-(tosyloxy)-2',5'-dioxa-1'-heptyl]benzene (19) with 1,3,5-tris(hydroxymethyl)benzene (5). Macrotricyclic quadruply bridged cyclophane crown ether 2 was obtained by a quadrupode-quadrupode coupling of 1,2,4,5-tetrakis(7'-tosyloxy-2,5'-dioxa-1'-heptyl)benzene (20) with 1,2,4,5-tetrakis(hydroxymethyl)benzene (6). These ligands could have suitable rigidity and cavity sizes for the coordination of metal cations. They appear to have selectivities for cesium over sodium and lead ions, and 2 shows a log K value of 3.50 for interaction with cesium ion in 80% CH3OH/20% water (v/v). Macrotricyclic polyether 2 containing benzene bridgeheads is a new type of ligand, and its structure was confirmed by an X-ray crystallographic study.

  DOI：

  10.1021/jo00079a013

文献信息

• Facile synthesis of benzene-bridged azaoxamacrobicyclic ligands
  作者：Jerald S. Bradshaw、Krzysztof E. Krakowiak

  DOI：10.1002/jhet.5570350305

  日期：1998.5

  complexation with anions have been prepared. Intermediate triamines were prepared in one-step using a triple Mitsonobu reaction, thereby shortening the overall synthetic sequence. A previously prepared benzene-bridged hexaazamacrocycle was prepared in only four-steps.

  已经制备了五种能够与阴离子络合的新型桶形大双环化合物。使用三重Mitsonobu反应一步一步制备中间体三胺，从而缩短了整体合成顺序。仅四步制备了先前制备的苯桥联的六氮杂大环。
• Novel benzene-bridged macrobi- and macrotricyclic polyethers
  作者：Haoyun An、Jerald S. Bradshaw、Krzysztof E. Krakowiak、Bryon J. Tarbet、N. Kent Dalley、Xiaolan Kou、Chengyue Zhu、Reed M. Izatt

  DOI：10.1021/jo00079a013

  日期：1993.12

  Novel three-dimensional benzene-bridged macrobicyclic polyether 1 and macrotricyclic polyether 2 have been prepared. Macrobicyclic triply bridged cyclophane crown compound 1 was synthesized by a tripode-tripode coupling of 1,3,5-tris[7'-(tosyloxy)-2',5'-dioxa-1'-heptyl]benzene (19) with 1,3,5-tris(hydroxymethyl)benzene (5). Macrotricyclic quadruply bridged cyclophane crown ether 2 was obtained by a quadrupode-quadrupode coupling of 1,2,4,5-tetrakis(7'-tosyloxy-2,5'-dioxa-1'-heptyl)benzene (20) with 1,2,4,5-tetrakis(hydroxymethyl)benzene (6). These ligands could have suitable rigidity and cavity sizes for the coordination of metal cations. They appear to have selectivities for cesium over sodium and lead ions, and 2 shows a log K value of 3.50 for interaction with cesium ion in 80% CH3OH/20% water (v/v). Macrotricyclic polyether 2 containing benzene bridgeheads is a new type of ligand, and its structure was confirmed by an X-ray crystallographic study.
• Synthesis of three-dimensionally arranged porphyrin arrays via intramolecular meso–meso coupling
  作者：Goro Mori、Naoki Aratani、Atsuhiro Osuka

  DOI：10.1016/j.tet.2007.05.075

  日期：2007.8

  reported. 1,3,5-Trioxamethylphenylene bridged Zn(II) porphyrin trimer 3 was coupled by Ag(I)-promoted oxidative coupling reaction to give porphyrin cage 5 comprising three meso–meso linked diporphyrins, which was then transformed by oxidation with DDQ and Sc(OTf)3 into porphyrin cage 7 comprising three fused diporphyrins. Intramolecular meso–meso coupling reaction was applied to porphyrin pentamer 11

  报道了通过空间电子通信的三维排列的卟啉阵列的合成和光物理性质。1,3,5-三氧杂甲撑亚苯基桥连的Zn（II）卟啉三聚体3通过Ag（I）促进的氧化偶联反应偶联，得到包含三个内消旋-内消旋二卟啉的卟啉笼5，然后用DDQ和Sc氧化将其转化（OTf）3进入包含三个稠合的双卟啉的卟啉笼7中。分子内内消旋-内消旋偶联反应应用于卟啉五聚体11，以提供卟啉阵列12由一个卟啉核心和两个介孔组成-介链的双卟啉。用DDQ和Sc（OTf）3进一步氧化12，得到三重堆叠的卟啉阵列13，其由两侧带有两个卟啉带的卟啉芯组成。UV-VIS-NIR吸收和荧光光谱的5，7，12，和13显示了堆叠的卟啉阵列内的扭曲构象和电子交互。